US2602803A - 2-acetoxytestosterone esters - Google Patents

2-acetoxytestosterone esters Download PDF

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Publication number
US2602803A
US2602803A US116622A US11662249A US2602803A US 2602803 A US2602803 A US 2602803A US 116622 A US116622 A US 116622A US 11662249 A US11662249 A US 11662249A US 2602803 A US2602803 A US 2602803A
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Prior art keywords
acetoxytestosterone
esters
mexico
testosterone
kaufmann
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Expired - Lifetime
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US116622A
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Kaufmann Stephen
Berlin Juan
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Syntex SA
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Syntex SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Definitions

  • R is selected from the residue of any suitable fatty acid and preferably the lower fatty acids such as acetic, propionic, butyric or an aromatic acid such as benzoic, may bereacted with lead tetracetate in accordance with the following equation:
  • the reaction is performed in glacial acetic acid solution and the reaction mixture is heated to a temperature of about 100 C.
  • Example grams of testosterone acetate were dissolved in 150 cc. of glacial acetic acid and grams of lead tetracetate were added. The mixture was maintained at for two and a half hours and then poured into water. The resulting precipitate was filtered and recrystallized first from methanol and then from ethyl acetate. The pure A*-androsten-2,17-diol-3-one-diacetate melted at 202-204" C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented July 8, 1952 Z-ACETOXYTESTOSTERONE ESTERS Stephen Kaufmann, George Rosenkranz, and Juan Berlin, Mexico City, Mexico, assignors to Syntex, S. A., Mexico City, Mexico, a corporation of Mexico N Drawing. Application September 19, 1949, Serial No. 116,622
2 Claims. (Cl. 260-397.4)
CH3 CH3 wherein R is selected from the residue of any suitable fatty acid and preferably the lower fatty acids such as acetic, propionic, butyric or an aromatic acid such as benzoic, may bereacted with lead tetracetate in accordance with the following equation:
Preferably, as indicated above, the reaction is performed in glacial acetic acid solution and the reaction mixture is heated to a temperature of about 100 C.
The following specific example serves to illustrate but is not intended to limit the present invention:
Example grams of testosterone acetate were dissolved in 150 cc. of glacial acetic acid and grams of lead tetracetate were added. The mixture was maintained at for two and a half hours and then poured into water. The resulting precipitate was filtered and recrystallized first from methanol and then from ethyl acetate. The pure A*-androsten-2,17-diol-3-one-diacetate melted at 202-204" C.
It will be obvious to those skilled in the art that various changes may be made without departing from the spirit of the invention and therefore the invention is not limited to what is described in the specification but only as indicated in the appcndedclaims.
We claim:
1. An ester of testosterone substituted in position 2: by an acetoxy group having the following formula:
CH: CH:
AcO
STEPHEN KAUFMANN. GEORGE ROSENKRANZ. JUAN BERLIN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,230,772 Bockmuhl Feb. 4, 1941 2,348,221 Logemann May 9, 1944 2,440,874 Reichstein May 4, 1948

Claims (1)

1. AN ESTER OF TESTOSTERONE SUBSTITUTED IN POSITION 2 BY AN ACETOXY GROUP HAVING THE FOLLOWING FORMULA:
US116622A 1949-09-19 1949-09-19 2-acetoxytestosterone esters Expired - Lifetime US2602803A (en)

Priority Applications (1)

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US2602803A true US2602803A (en) 1952-07-08

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762818A (en) * 1955-05-26 1956-09-11 Searle & Co 4-hydroxytestosterone and esters thereof
US2805231A (en) * 1956-06-06 1957-09-03 Searle & Co 1-hydroxy-4-androstene-3, 17-dione and esters thereof
US2847428A (en) * 1955-10-27 1958-08-12 Sterling Drug Inc Pregnan-2-oil-3, 20-dione, allopregnan-2-ol-3, 20-dione, esters thereof, and preparation thereof
US3063989A (en) * 1960-01-18 1962-11-13 American Cyanamid Co 2beta-hydroxy-9 alpha-halo-11-oxygenated pregnenes
US3063991A (en) * 1960-12-07 1962-11-13 American Cyanamid Co 2-hydroxy-9alpha-fluoro pregnenes and pregnadienes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2230772A (en) * 1937-07-05 1941-02-04 Winthrop Chem Co Inc Process of preparing substances having the efficacy of the cortical hormone or intermediate products for the preparation of such substances
US2348221A (en) * 1938-12-24 1944-05-09 Schering Corp Hydroxyl derivatives of the cyclopentano polyhydrophenanthrene series and a process for the manufacture of the same
US2440874A (en) * 1942-10-07 1948-05-04 Reichstein Tadeus Compounds of the adrenal cortical hormone series and process of making same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2230772A (en) * 1937-07-05 1941-02-04 Winthrop Chem Co Inc Process of preparing substances having the efficacy of the cortical hormone or intermediate products for the preparation of such substances
US2348221A (en) * 1938-12-24 1944-05-09 Schering Corp Hydroxyl derivatives of the cyclopentano polyhydrophenanthrene series and a process for the manufacture of the same
US2440874A (en) * 1942-10-07 1948-05-04 Reichstein Tadeus Compounds of the adrenal cortical hormone series and process of making same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762818A (en) * 1955-05-26 1956-09-11 Searle & Co 4-hydroxytestosterone and esters thereof
US2847428A (en) * 1955-10-27 1958-08-12 Sterling Drug Inc Pregnan-2-oil-3, 20-dione, allopregnan-2-ol-3, 20-dione, esters thereof, and preparation thereof
US2805231A (en) * 1956-06-06 1957-09-03 Searle & Co 1-hydroxy-4-androstene-3, 17-dione and esters thereof
US3063989A (en) * 1960-01-18 1962-11-13 American Cyanamid Co 2beta-hydroxy-9 alpha-halo-11-oxygenated pregnenes
US3063991A (en) * 1960-12-07 1962-11-13 American Cyanamid Co 2-hydroxy-9alpha-fluoro pregnenes and pregnadienes

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